Diego Simeone is considered one of the most frequently faced coaches against Real Madrid in history, having led Atlético Madrid in 45 matches against the prestigious neighbor, achieving 12 victories, alongside 17 draws and 16 defeats, with his team scoring 48 goals while conceding 66 goals.

Despite Real Madrid's overall superiority, Simeone has achieved memorable victories, the most notable being:

2013 Copa del Rey Final: He led Atlético Madrid to a 2-1 victory at Santiago Bernabéu, ending a 14-year drought without a win against the royal club.

2018 UEFA Super Cup: He won with a score of 4-2, securing a European title at the expense of Real Madrid.

2020/2021 La Liga: He successfully led Atlético Madrid to win La Liga after fierce competition with Real Madrid and Barcelona.

On the other hand, the UEFA Champions League encounters have been more painful for Simeone against Real Madrid, having lost two finals:

2014 Final: A dramatic defeat after Sergio Ramos' last-minute goal in the 93rd minute, followed by Atlético Madrid losing 4-1 after extra time.

2016 Final: Lost on penalties after a 1-1 draw.

2015 Quarter-Final: Defeat and elimination from the tournament.

2017 Semi-Final: Suffered a heavy defeat of 3-0 due to a Cristiano Ronaldo hat-trick, and despite winning 2-1 in the return leg, he was eliminated from the tournament.

Simeone faced his counterpart Carlo Ancelotti in 26 matches, managing to defeat him 9 times, while the Italian coach achieved the same number of victories, and 8 matches ended in a draw. Despite Ancelotti's attacking squad, Simeone has always found a way to impose his solid defensive style, making their encounters one of the most complex tactical clashes in modern football.